Jump to main content
Jump to site search

Issue 1, 2007
Previous Article Next Article

Exploring the chemistry of penicillin as a β-lactamase-dependent prodrug

Author affiliations

Abstract

The penam nucleus can be modified to behave as a β-lactamase-dependent ‘prodrug’ by incorporation of a vinyl ester side chain at the 6-position. Enzyme-catalysed hydrolysis of the β-lactam ring uncovers the thiazolidine-ring nitrogen as a nucleophile that drives a rapid intramolecular displacement on the side chain. Attachment of 7-hydroxy-4-methylcoumarin as the releasable group of this side chain generated a penicillin structure that can function as a fluorescence-based reporter substance/diagnostic for the presence of low levels of β-lactamase enzyme in solution. Mechanistic details of the reaction pattern are documented and the scope and limitations of exploiting the structural modification are discussed.

Graphical abstract: Exploring the chemistry of penicillin as a β-lactamase-dependent prodrug

Back to tab navigation

Supplementary files

Article information


Submitted
10 Oct 2006
Accepted
08 Nov 2006
First published
22 Nov 2006

Org. Biomol. Chem., 2007,5, 160-168
Article type
Paper

Exploring the chemistry of penicillin as a β-lactamase-dependent prodrug

C. C. Ruddle and T. P. Smyth, Org. Biomol. Chem., 2007, 5, 160 DOI: 10.1039/B614758E

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.


Social activity

Search articles by author

Spotlight

Advertisements